Towards enantiopure macrocyclic trans-dinucleating hemilabile P-Alkene ligands: Syntheses, structures, and Chiral Pd-Complexes

Frieß S, Herrera AC, Linden A, Heinemann FW, Dorta R (2019)

Publication Type: Journal article

Publication year: 2019

Journal

Book Volume: 898

Article Number: 120876

DOI: 10.1016/j.jorganchem.2019.120876

Abstract

Dibenzazepinyl dichlorophosphine 2 reacts with (R,R)-2,3-O-isopropylidene-threitol (3) in Et2O solution to afford gram-quantities of the enantiopure macrocylic phosphoramidite (all-R)-6, which may be seen as a formal dimer of classic phosphoramidite P-alkene hybrid ligands. Complexation experiments with PdCl2 reveal highly selective formation of the trans-dinuclear complex (all-R)-11. The corresponding bulkier and rigidly trans-eclipsed 1,4-diol (S,S)-bis-hydroximethyl-9,10-dihydro-9,10-ethaneanthracene (4) does not favor macrocycle formation and exclusively leads to the new dibenzazepinyl phsophormaidite P-alkene ligand 7, which in Pd-catalyzed asymmetric allylic amination comes the well-known ‘privileged’ binol-derived P-alkene analogue 1 close in terms of enantioselection.

Authors with CRIS profile

Involved external institutions

University of Zurich / Universität Zürich (UZH) Switzerland (CH)

How to cite

APA:

Frieß, S., Herrera, A.C., Linden, A., Heinemann, F.W., & Dorta, R. (2019). Towards enantiopure macrocyclic trans-dinucleating hemilabile P-Alkene ligands: Syntheses, structures, and Chiral Pd-Complexes. Journal of Organometallic Chemistry, 898. https://dx.doi.org/10.1016/j.jorganchem.2019.120876

MLA:

Frieß, Sibylle, et al. "Towards enantiopure macrocyclic trans-dinucleating hemilabile P-Alkene ligands: Syntheses, structures, and Chiral Pd-Complexes." Journal of Organometallic Chemistry 898 (2019).

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